I like signed FDC's and event covers. Between envelopes and postal cards I have over 100. They are quite predominant for Olympic athletes
The basketball collection is nice. Back in the 1980's and early 1990's you could go to the Basketball HOF and buy the 1961 covers signed by HOFers for $6 each. This included some that died in the 1960's and 1970's (Ed Wachter, Ralph Morgan, Dave Tobey) and two players who participated in the first game (Ernest Hildner, Raymond Kaighn). I only purchased one of each though I should have bought more. When Ed 'Moose' Krause died I was working at the courthouse in Springfield and did go in and buy more, but that was the only time.
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A friend got the top one signed by Penny Pitou (1960 silver medal skiing) for me in Switzerland when he had lunch with her. I got the bottom one signed in person in Sweden at the World Olympic Collector's Fair.
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I got both of these in person at the World Olympic Collector's Fair in Sweden.
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The other Cy Young. These are postal cards.
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Sam Graddy won a gold medal in 1984. He also played in the NFL. The Italian Postal Authority or the Italian Olympic Committee issued a set of envelopes for each gold medal individual or team. I have gotten a few signed. Peter Snell competed for New Zealand but spent many years as a research scientist at the University of Texas.
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Souvenir sheets also look nice signed, especially when the athlete is depicted.
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Two covers where the athlete is depicted on the stamp. Capilla is a 1956 Olympic champion stamp from the Dominican Republic. Stukelj is on a stamp from Slovenia.
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One of the few U.S. stamps that depicts a living person. LeConey, 1924 gold medalist in the 4x100m relay, posed for this stamp which was used as a fundraiser for the 1932 Olympics.